Chiral triazole pesticides may cause enantioselectively adverse effects to non-target organisms. In this work, we employed zebrafish as an aquatic organism model to explore stereoselective acute toxicity, bioaccumulation, oxidative stress, and thyroid disruption of cis-metconazole enantiomers. The median lethal concentration values of (1S, 5R)-metconazole, (1R, 5S)-metconazole, and the mixture of them against zebrafish were 4.01, 2.61 and 3.17 mg⋅L⁻¹, respectively. (1R, 5S)-Metconazole was preferentially bioaccumulated in zebrafish than (1S, 5R)-metconazole, and the bioconcentration factor of (1R, 5S)-metconazole was 1.28-fold larger than that of (1S, 5R)-metconazole. Then, the activity order of catalase, superoxide dismutase, and glutathione-S transferase enzymes in zebrafish was expressed as (1S, 5R)-metconazole > the mixture > (1R, 5S)-metconazole, while the order of malondialdehyde content in zebrafish was (1R, 5S)-metconazole > the mixture > (1S, 5R)-metconazole. Moreover, cis-metconazole exhibited enantioselective regulation effects on the levels of triiodothyronine and thyroxine in zebrafish, and (1R, 5S)-metconazole possessed stronger thyroid disruption ability to zebrafish than the others. By virtue of molecular docking methodology, the binding affair and docking energy results supported that interactions between (1R, 5S)-metconazole and thyroid hormone receptors were much stronger than those between (1S, 5R)-metconazole and same receptors. This study of enantioselective evaluation of cis-metconazole in zebrafish can provide favorable information for risk assessments of chiral pesticides toward environment and health of aquatic organisms.

手性三唑类农药可能对非靶标生物造成对映选择性的不利影响。在这项工作中，我们采用斑马鱼作为水生生物模型来探索顺式-甲康唑对映体的立体选择性急性毒性、生物蓄积性、氧化应激和甲状腺破坏。(1 S , 5 R )-metconazole、(1 R , 5 S )-metconazole 及其混合物对斑马鱼的中位致死浓度值分别为4.01、2.61 和3.17 mg·L ^-1。(1 R , 5 S )-Metconazole 在斑马鱼中的生物累积优先于 (1 S , 5 R)-metconazole，(1 R , 5 S )-metconazole 的生物富集因子是 (1 S , 5 R )-metconazole的 1.28 倍。则斑马鱼中过氧化氢酶、超氧化物歧化酶和谷胱甘肽-S转移酶的活性顺序为(1 S , 5 R )-metconazole > the mix > (1 R , 5 S )-metconazole , 而丙二醛的顺序为斑马鱼中的含量为(1 R , 5 S )-metconazole > 混合物 > (1 S , 5 R )-metconazole 。此外，顺式-metconazole对斑马鱼三碘甲状腺原氨酸和甲状腺素水平具有对映选择性调节作用，(1 R , 5 S )-metconazole对斑马鱼甲状腺的破坏能力强于其他。借助分子对接方法，结合事件和对接能结果支持(1 R , 5 S )-metconazole 与甲状腺激素受体之间的相互作用比(1 S , 5 R )-metconazole 和相同受体之间的相互作用强得多。本研究对顺式的对映选择性评价斑马鱼中的甲康唑可以为手性农药对环境和水生生物健康的风险评估提供有利信息。